Similar to my Boston Bucket List, while I’m living in Chicago, I’d like to make the most of my time in this lovely windy city.

  1. Visit the Signature Room at the Hancock Tower and the observatory at the Sears Tower.
  2. Fully experience the Taste of Chicago.
  3. Visit the Garfield Park Conservatory, the Chicago Botanic Gardens, and the Morton Arboretum.
  4. Go on the Chicago architectural boat tour.
  5. Attend a Cubs game at Wrigley Field and a Sox game at Comiskey Park.
  6. Eat authentic local food at Greektown, Pilsen, Little Italy, and Chinatown.
  7. Try the climbing wall at Maggie Daley park.
  8. Go ice skating at Millenium Park and at Maggie Daley park.
  9. Bike ride along the 606.
  10. Soar among the sky scrapers on a helicopter tour of the city.
  11. Catch a free concert in Millenium Park.
  12. Watch a free outdoor movie in Millenium Park.
  13. Attend a free zumba lesson in Millenium Park.
  14. Watch a live-taping of Wait, Wait, Don’t Tell Me.
  15. Attend Lollapallooza, Pitchfork or the Ravinia music festival.
  16. Catch a comedy show at Second City and IO.
  17. Listen to jazz at Green Mill.
  18. Visit all of Chicago’s major museums: Art Institute, Field Museum, Shedd Aquarium, Adler Planetarium, Museum of Science and Industry.
  19. Visit all of Chicago’s less well-known museums: Museum of Contemporary Art,
  20. Take a long walk down the lakefront trail.
  21. Catch a show at the Lyric Opera.
  22. Eat at Alinea and Girl and the Goat.
  23. See the sunrise from Montrose Point or Promontory Point.
  24. Get dessert at the Nutella cafe.
  25. Play volleyball on one of the Lake Michigan beaches.
  26. Check out a Bulls, Blackhawks, and Bears game.
  27. Ride the CTA holiday train.
  28. Attend the Lincoln Park weekend farmer’s market.
  29. Ride the ferris wheel at Navy Pier.
  30. Watch the Fourth of July, New Year’s Eve, and weekly summer fireworks at Navy Pier.
  31. Attend an After Dark event at the Art Institute, Adler Planetarium, and Lincoln Park Zoo.
  32. Go sailing on Lake Michigan, in an actual sailboat.
  33. Check out the Air and Water show.
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